Sounds like daunting task.

There are multiple considerations here beyond managing reservations and cleanings and if you only have one property I think you will find it cost prohibitive and creating other challenges. 

I'm a Newbie to real estate investing, super excited and abit anxious about the challenge of getting started(beginner nerves I guess).I'm diving in because I want to acheive financial independence for my family through passive income.

And I probably know exactly the thoughts, challenges, questions, and information overload, etc. that you might be feeling and experiencing right now.And I know the "iceberg" and the "elephant" seem very daunting right now.What helped me go from buying a duplex to buying 100+ unit deals is boiling down this business into 2 simple things, Deals and Dollars.I share more of this approach in a thread if you want to read, I quit my CPA Job to buy Large Apartment BuildingsTo summarize though, the road ahead for you will most likely have many twists and turns, challenges and setbacks.

Getting into my first deal has been challenging, but I'm forging ahead.  

I know my journey will probably be long and hard but I haven't felt this passionate about anything like this in my life, so I'm ready for the challenges and rewards. 

I'm excited about the challenges to come and the stories to tell.

Good luck getting into this challenging but exciting market!

I did try to challenge a higher reassessment this year on two of my properties and they just said that if I paid x amount, the properties must have been worth it and assessments should reflect that. 

Sounds like you have great conviction in the cause, that will help you out when you hit any challenges or bumps in the road.